Trippier was born in Bury and joined the Manchester City ranks in 1999, aged just nine as took his first steps towards a career which would see him become an England star.
The right back spent 13 years on the City books, but failed to even make his debut for the club, and was loaned out to Barnsley and Burnley before joining the latter permanently in 2012.
In three years with the Clarets, Trippier impressed as an attack-minded right back, and he earned a move to Tottenham in 2015 even after Burnley were relegated back to the Championship.
Trippier, 27, has kicked on again with Spurs, not only becoming Mauricio Pochettino's first-choice right back but also a regular for England, emerging from this summer's World Cup as one of the stars for the Three Lions.
Now earning £65,000-a-week at Spurs (Daily Mail), Trippier has come a long way since being let go by City – and it seems that there is some regret over that deal at the Etihad Stadium.
A City source has told the Daily Mail that Trippier 'got lost in the system and should never have gone', and possibly, in an ideal world, Trippier would have wanted to have made the grade with City.
Burnley and Tottenham have been the ones to benefit in recent years, and City will be hoping to make better decisions on their young talents in the coming years.